4-(1-Ethyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine → 4-[1-ethyl-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-3-yl]aniline
Reaction equation
[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][CH:15]=[CH:16][C:9]=23)[C:5]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=2)=[N:4]1)[CH3:2]>C(O)(=O)C.[Zn]>[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][CH:15]=[CH:16][C:9]=23)[C:5]([C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=2)=[N:4]1)[CH3:2]Participants
4
Procedure
A solution of 4-[1-ethyl-3-(4-nitrophenyl)-1H-pyrazol-4-yl]-1H-pyrrolo[2,3-b]pyridine (59 mmol) in glacial acetic acid (25 mL) was treated with zinc dust (41 mmol) and stirred for 1 h at room temperature. The reaction was then filtered and concentrated in vacuo. The resultant residue was suspended in a 1:1 solution of ethyl acetate (10 mL) and saturated sodium bicarbonate (10 mL) and stirred 30 minutes. The organic layer was separated, filtered, washed with brine (1×5 mL), dried over sodium sulfate, and concentrated. Purification of the residue by flash chromatography (80-100% ethyl acetate/hexanes) provided the title product as a white powder (85%). ESMS [M+H]+: 304.2
Workup
- filtrationThe reaction was then filtered
- concentrationconcentrated in vacuo
- stirringstirred 30 minutes
- customThe organic layer was separated
- filtrationfiltered
- washwashed with brine (1×5 mL)
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- customPurification of the residue by flash chromatography (80-100% ethyl acetate/hexanes)
Sources & evidence
- ORD record
- ord-ac5dfc50456c41a2ad67373f66215fb3
- Source dataset
- uspto-grants-2007_10
- Patent number
- US07282588B2
Reaction notes
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